Vegetable oil-maleic anhydride and maleimide derivatives: Syntheses and properties

Abstract

The marriage of maleic anhydride and vegetable oils as a unique class of environmentally benign macromonomers and sustainable polymers has attracted a great deal of interests in the last few decades. The rich chemistry and versatile reactivity of maleic anhydride, combined with the biodegradable and renewable nature of vegetable oils, have rendered infinite possibilities for the maleic anhydride-vegetable oil derivatives. This section provides a survey of the recent literatures on the synthetic routes of the various maleic anhydride derivatives based on the reactive sites in the vegetable oil, as well as the properties and applications of these novel macromonomers and polymers. Maleimides and derivatives are important building blocks in chemical synthesis, and some of them demonstrate biological activity. A special feature of the reactivity of maleimides is their susceptibility to additions across the double bond, either by Michael additions or via Diels-Alder reactions. The carbon-carbon double bond in maleimide is also capable of free-radical or anionic polymerization or copolymerization to produce functional polymers that are utilized in high temperature applications, such as adhesives in the semiconductor industry. Biological applications of maleimide derivatives result from their high and specific reactivity/binding toward the thiol groups in biological substrate (e.g., chemical probes), site-directed modification for proteins and peptides, bioconjugates, and prodrugs.